I totally get where you're coming from! The Caribbean can be pricey, but there are definitely some more budget-friendly options out there. I've done a bit of traveling around the region on a tight budget, so here are a few islands that you might want to consider:
Dominican Republic: It's known for having affordable options when it comes to accommodation and food. If you explore beyond the all-inclusive resorts, you'll find a range of budget hotels and guesthouses. Local eateries offer delicious meals at a fraction of the price you’d pay at tourist spots.
Puerto Rico: Because it's a U.S. territory, flights can sometimes be cheaper, especially if you're flying from the mainland U.S. You can find budget accommodations in San Juan, and there are plenty of free or inexpensive activities, like exploring the beaches or hiking in El Yunque National Forest.
Jamaica: If you stay away from the major resort areas, you can find affordable places. Negril and the South Coast have some budget-friendly accommodations and beautiful beaches. You can enjoy local jerk chicken stands that are both tasty and easy on the wallet.
Cuba: Although it requires a bit more planning due to travel restrictions, it can be extremely budget-friendly. You can stay in casas particulares (private homes), which are a great way to experience local culture. Plus, the street food is inexpensive and delicious.
As for flights, I use search engines like Skyscanner or Google Flights to monitor prices and set alerts for the best deals. Traveling during the shoulder season can also save you money. For transport on the islands, public transportation or shared taxis (where available) can be cost-effective alternatives to renting a car.
I hope this helps, and you have a great time planning your Caribbean adventure! If you're looking for more in-depth tips, there are blogs and travel guides dedicated to budget travel in the Caribbean that could offer additional insights.